3.4-dioxyphenyl-1-alkylendiamin-1.2 and process of making same.



ERNST GRETHER, 01 DETROIT.

MICHIGAN. ASSIGNOR. BY MESNE ASSIGNMENTS, TO

ADAM BET/TING, 01* DETROIT. MICHIGAN.

SA-DIOXYPHENYL'l-ALKYLENDIAMIN-1.2 AND PROCESS OF MAKING SAME.

momma.

No Drawing. Application filed July 16, 1906.

Specification of Letters Patent.

Serial No. 326.301.

.llatcnted Jan. 728, .1913.

(Specimens) To a 'le/ioor '1 If m w concern lle it. known that l, lluxs'r liRETI-IER. a subject. ot the Emperor of Germany. residing at Detroit, in the county of ll'ayne aml State oil Michigan, have invented certain new and useful lnn')rovemcnts in 3. l )ioxyphenyl-l-alkylendiamin-l.9 and Processes of Making Same of which the followinc is a specification.

This invention relates to substances having blood pressure raising properties that are obtained by reduction from 3.--.l-i,lioxyphcuylglyoxims which form the subject matter of a renewed prior application Serial No. 6715653. If these last named sub stances which corresporul to the general tori it ill a the formula.

-- (,i--:ilkyl:nmn

Nl'lg These new products possess in a marked degree the property of increasing the pressure of blood sinnlar to adrenalin and while equally effective are less tox c than the lattcr.

The following example illustrates how the invention mzy be practised: 20 g. of the 3.el-dioxyphenylglyoxim are dissolved in i000 g. warm water and while being cooled with ice are reduced with M5 g. sodium amalgam of 2.91% of sodium and 77 g. of hydrochloric acid of 10.5% strength. The addition 0* the sodium amalgam and the hydrochloric acid is made in small portions during about hours the solution being kept slightly acid all the time and vigorously stirred up. After the fluid is decanted are obtained which coiy from the mercury it is neutralized with sodium bicarbonate, litmus being used as an indicator. 7

By diluting the liquid to about ooo cc. a solution of thr active sub lance is obtained which is applicable without 'l'urlhcr manipulation and according: to physiological tests produces L'LSdllr: on a par with that ol' adrenalin in a l l lllt solution.

Instead of the lrvdrochloric acid other acids may be substituted but the use of the former is especially appropriate] as it gives rise to the formation ol'; sodium chlorid the presence of which is desirable 'i'or subcutaneous u e and for imparting greater stability to the solution.

The effective bases have as yet not been obtained in a free state. The color of the acid solution is colorless to yellow, it pro duces with ferric chlorid in very diluted torm an intense green color, and by the addition of free alkali the color of the solul'ion turns to brown. in its pllyHlOlUfgh'ul elt'ect it behaves like adrenalin by contracting; the blood vessels and it also reduces the toxic action of local anesthetics when injccted therewith. Similarly eltectire products are obtained by reduction with amalgam ot' the 3.-'l -dioxyphenylmethylglyoxim described in the above mentioned application Serial No. (371565.

\Vhat I. claim is:-

1. The process of making a EBA-dim phenyl-Lalkylcndiamiii-l.9 which consists in sulfijecting 3.4-dioxyphcnyl-l-glyoxim to reduction with suitable metal amalgams in presence of acids substantially as described.

2. The process of making a 3.-l-dio.\'yphenyl-l-alkylcndiamiu-l.2 which consists in subjecting Set-dioxyphenybl-glyoxims to reduction with sodium amalgam in presence of hydrochloric acid. substantially as described.

3. As a new product the 3.4-dioxypheuyll-alkylendiamin corresponding to the formula.

-=--G-alkylamin H2 in which the two amin groups are attached to adjacent carbon atoms, and which is in In testimony whereof I aflix my signature theform of a salt solution the active prinin presence of two witnesses.

ciple 01' base of which has bleed pressure raising qualities and which is characterized ERNST GRETHER. by being colorless to yellow producing with ferric chlorid in a diluted form an intense Witnesses:

green color, andwith the addition of a free OTTO F. BARTI-LEL,

alkali a brown color. CHAS. B. SH'UMWAY. 

